Liquoric acid (CHEM028539)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:31:40 UTC
Update Date2016-11-09 01:18:42 UTC
Accession NumberCHEM028539
Identification
Common NameLiquoric acid
ClassSmall Molecule
DescriptionMinor constituent of liquorice root (Glycyrrhiza glabra). Liquoric acid is found in tea and herbs and spices.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
LiquateGenerator
Liquic acidGenerator
16,21-Epoxy-3-hydroxy-11-oxo-12-oleanen-30-Oic acidHMDB
Licoric acidHMDB
(1R,3S,4R,9S,12S,17S,19R,20R,22S)-9-Hydroxy-3,4,8,8,12,19,22-heptamethyl-14-oxo-23-oxahexacyclo[18.2.1.0³,¹⁶.0⁴,¹³.0⁷,¹².0¹⁷,²²]tricos-15-ene-19-carboxylateGenerator
Chemical FormulaC30H44O5
Average Molecular Mass484.667 g/mol
Monoisotopic Mass484.319 g/mol
CAS Registry NumberNot Available
IUPAC Name(1R,3S,4R,9S,12S,17S,19R,20R,22S)-9-hydroxy-3,4,8,8,12,19,22-heptamethyl-14-oxo-23-oxahexacyclo[18.2.1.0³,¹⁶.0⁴,¹³.0⁷,¹².0¹⁷,²²]tricos-15-ene-19-carboxylic acid
Traditional Name(1R,3S,4R,9S,12S,17S,19R,20R,22S)-9-hydroxy-3,4,8,8,12,19,22-heptamethyl-14-oxo-23-oxahexacyclo[18.2.1.0³,¹⁶.0⁴,¹³.0⁷,¹².0¹⁷,²²]tricos-15-ene-19-carboxylic acid
SMILES[H][C@@]12C[C@](C)([C@H]3C[C@]1(C)[C@@H](C[C@]1(C)C2=CC(=O)C2[C@@]4(C)CC[C@H](O)C(C)(C)C4CC[C@@]12C)O3)C(O)=O
InChI IdentifierInChI=1S/C30H44O5/c1-25(2)19-8-11-29(6)23(26(19,3)10-9-20(25)32)18(31)12-16-17-13-28(5,24(33)34)21-14-27(17,4)22(35-21)15-30(16,29)7/h12,17,19-23,32H,8-11,13-15H2,1-7H3,(H,33,34)/t17-,19?,20-,21+,22+,23?,26-,27-,28+,29+,30+/m0/s1
InChI KeyNGWKGSCSHDHHAJ-YPFQVHCOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Naphthofuran
  • Cyclohexenone
  • Oxepane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0027 g/LALOGPS
logP4.24ALOGPS
logP4.73ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.24ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.79 m³·mol⁻¹ChemAxon
Polarizability55.37 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-0326900000-48d437fc747bc9d921f2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2042429000-27682d63c2bc6a27d445Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0000900000-dd448cd448ce7d0f4004Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bj-0010900000-eb785e7b2bf0a7f01521Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-3666900000-f6056144c9dac067fb89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-128f39741dfad7baae41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0080-0000900000-c02d82ea232e457b67baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0001900000-b6be20c58a77bc078449Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-424bba629934fef50ccdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000900000-34775030bf8ee283f0a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0016-4000900000-e05ddebed334712f8cdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-b935d139a68c7b2c6e60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0001900000-a214846e7e9419a8cf19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-2459700000-c1898abd2b7789971c2eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034512
FooDB IDFDB013012
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751571
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM